JP2002541308A5 - - Google Patents
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- JP2002541308A5 JP2002541308A5 JP2000610306A JP2000610306A JP2002541308A5 JP 2002541308 A5 JP2002541308 A5 JP 2002541308A5 JP 2000610306 A JP2000610306 A JP 2000610306A JP 2000610306 A JP2000610306 A JP 2000610306A JP 2002541308 A5 JP2002541308 A5 JP 2002541308A5
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- molar ratio
- diol
- polylactic acid
- isocyanate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 150000002009 diols Chemical class 0.000 description 16
- 229920000747 poly(lactic acid) Polymers 0.000 description 16
- 239000004626 polylactic acid Substances 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical group NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 11
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 10
- 239000012948 isocyanate Substances 0.000 description 10
- 150000002513 isocyanates Chemical class 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 229920002307 Dextran Polymers 0.000 description 7
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- 150000004676 glycans Chemical class 0.000 description 6
- 229920001282 polysaccharide Polymers 0.000 description 6
- 239000005017 polysaccharide Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 229920001477 hydrophilic polymer Polymers 0.000 description 5
- 230000002209 hydrophobic effect Effects 0.000 description 5
- 229920005615 natural polymer Polymers 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 229920001059 synthetic polymer Polymers 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 229920006037 cross link polymer Polymers 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 3
- 230000037431 insertion Effects 0.000 description 3
- 238000003780 insertion Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 102000004196 processed proteins & peptides Human genes 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VJLOFJZWUDZJBX-UHFFFAOYSA-N bis(2-hydroxyethyl)azanium;chloride Chemical compound [Cl-].OCC[NH2+]CCO VJLOFJZWUDZJBX-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical class NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 0.000 description 2
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical group CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920001184 polypeptide Polymers 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 102000003974 Fibroblast growth factor 2 Human genes 0.000 description 1
- 108090000379 Fibroblast growth factor 2 Proteins 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- 102000000589 Interleukin-1 Human genes 0.000 description 1
- 108010002352 Interleukin-1 Proteins 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 102000016943 Muramidase Human genes 0.000 description 1
- 108010014251 Muramidase Proteins 0.000 description 1
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 1
- 241001655798 Taku Species 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- -1 isocyanatoethyl Chemical group 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 239000004325 lysozyme Substances 0.000 description 1
- 229960000274 lysozyme Drugs 0.000 description 1
- 235000010335 lysozyme Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000004520 water soluble gel Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12880399P | 1999-04-12 | 1999-04-12 | |
| US60/128,803 | 1999-04-12 | ||
| PCT/US2000/006416 WO2000060956A1 (en) | 1999-04-12 | 2000-03-20 | Hydrogel-forming system with hydrophobic and hydrophilic components |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002541308A JP2002541308A (ja) | 2002-12-03 |
| JP2002541308A5 true JP2002541308A5 (enExample) | 2007-04-26 |
| JP4558213B2 JP4558213B2 (ja) | 2010-10-06 |
Family
ID=22437052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000610306A Expired - Fee Related JP4558213B2 (ja) | 1999-04-12 | 2000-03-20 | 疎水性および親水性の成分を有する水性ゲル形成システム |
Country Status (10)
| Country | Link |
|---|---|
| US (4) | US6388047B1 (enExample) |
| EP (1) | EP1168934B1 (enExample) |
| JP (1) | JP4558213B2 (enExample) |
| AT (1) | ATE386075T1 (enExample) |
| AU (1) | AU3877200A (enExample) |
| CA (1) | CA2368617C (enExample) |
| DE (1) | DE60038010T2 (enExample) |
| DK (1) | DK1168934T3 (enExample) |
| ES (1) | ES2298135T3 (enExample) |
| WO (1) | WO2000060956A1 (enExample) |
Families Citing this family (83)
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| US6716445B2 (en) | 1999-04-12 | 2004-04-06 | Cornell Research Foundation, Inc. | Hydrogel entrapping therapeutic agent and stent with coating comprising this |
| CA2450123C (en) * | 2001-08-02 | 2013-01-29 | Cornell Research Foundation, Inc. | Biodegradable polyhydric alcohol esters |
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| BR0314266A (pt) * | 2002-09-13 | 2005-07-26 | Ocular Sciences Inc | Dispositivos e métodos para a melhora de visão |
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| CN106913915B (zh) * | 2017-04-21 | 2019-05-31 | 浙江大学 | 一种自愈合支架复合涂层及其制备方法和应用 |
| CN107216450B (zh) * | 2017-04-21 | 2019-06-11 | 浙江大学 | 一种自愈合抗菌涂层及其制备方法和应用 |
| US10975121B2 (en) | 2017-06-24 | 2021-04-13 | Cytogel Pharma, Llc | Analgesic mu-opioid receptor binding peptide pharmaceutical formulations and uses thereof |
| CN110108537B (zh) * | 2018-02-01 | 2020-08-25 | 中国科学技术大学 | 一种用于生物组织包埋的包埋剂和包埋方法 |
| CN108359054A (zh) * | 2018-02-10 | 2018-08-03 | 西北大学 | 一种葡萄糖敏感型全互穿网络水凝胶及其制备方法 |
| CN116496475B (zh) * | 2023-06-26 | 2023-09-22 | 海杰亚（北京）医疗器械有限公司 | 用于栓塞微球的可降解交联剂、可降解栓塞微球及其制备方法和药物组合物 |
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2000
- 2000-03-20 DE DE60038010T patent/DE60038010T2/de not_active Expired - Lifetime
- 2000-03-20 EP EP00917865A patent/EP1168934B1/en not_active Expired - Lifetime
- 2000-03-20 DK DK00917865T patent/DK1168934T3/da active
- 2000-03-20 JP JP2000610306A patent/JP4558213B2/ja not_active Expired - Fee Related
- 2000-03-20 US US09/531,451 patent/US6388047B1/en not_active Expired - Lifetime
- 2000-03-20 CA CA2368617A patent/CA2368617C/en not_active Expired - Fee Related
- 2000-03-20 ES ES00917865T patent/ES2298135T3/es not_active Expired - Lifetime
- 2000-03-20 AT AT00917865T patent/ATE386075T1/de not_active IP Right Cessation
- 2000-03-20 WO PCT/US2000/006416 patent/WO2000060956A1/en not_active Ceased
- 2000-03-20 AU AU38772/00A patent/AU3877200A/en not_active Abandoned
-
2002
- 2002-03-13 US US10/096,435 patent/US6583219B2/en not_active Expired - Fee Related
-
2003
- 2003-02-21 US US10/369,676 patent/US6709668B2/en not_active Expired - Fee Related
- 2003-12-12 US US10/733,291 patent/US6916857B2/en not_active Expired - Fee Related
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